Department of Chemistry, Christopher Ingold Laboratories, University College London, 20 Gordon Street, London WC1H 0AJ, U.K.
Org Lett. 2021 Apr 2;23(7):2488-2492. doi: 10.1021/acs.orglett.1c00424. Epub 2021 Mar 17.
Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions.
糖在废生物质中含量丰富，是有机合成中可持续的手性构建块。由于手性饱和杂环在药物应用中提供了明确的三维框架，显示出增加的代谢抗性，因此对其的需求正在增加。在温和的碱性条件下，可以选择性地在 C-2 位脱水一系列糖硫缩醛，得到的烯酮硫缩醛可以通过进一步的选择性脱水反应应用于生产有用的手性构建块。
